Private jet cost · Chicago, IL
Private jet flights to Chicago
Into Chicago we price private jet flights from 163 cities, from Indianapolis (162 miles, about 40 minutes) to Kauai (4,291 miles). 133 are nonstop in a light jet and 159 in a super-midsize like the Challenger 350, the longest being Anchorage to Chicago. 60 cross a border.
Every figure is an estimate from published jet card rates, checked October 2, 2026, times the flight time. Open a route for every option and what the estimate leaves out.
Every route to Chicago
One-way estimates by jet size: the middle half of published hourly rates times the flight time, before minimums and fees. Flight time is for the jet size each trip usually calls for; a dash means a size can't practically fly it.
Midwest9 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Indianapolis to ChicagoIndianapolis, IN162 mi · 40m light | 162 mi | 40mlight | $5k–$6k | $6k–$6.5k | $7k–$8k | $8.5k–$9.5k | $5k–$6k |
| Detroit to ChicagoDetroit, MI228 mi · 50m light | 228 mi | 50mlight | $6k–$7.5k | $7.5k–$8k | $8.5k–$10k | $10k–$11.5k | $6k–$7.5k |
| Cincinnati to ChicagoCincinnati, OH249 mi · 50m light | 249 mi | 50mlight | $6.5k–$8k | $8k–$8.5k | $9k–$10.5k | $10.5k–$12k | $6.5k–$8k |
| St. Louis to ChicagoSt. Louis, MO251 mi · 50m light | 251 mi | 50mlight | $6.5k–$8k | $8k–$8.5k | $9.5k–$10.5k | $10.5k–$12k | $6.5k–$8k |
| Columbus to ChicagoColumbus, OH282 mi · 55m light | 282 mi | 55mlight | $7k–$8.5k | $8.5k–$9k | $10k–$11.5k | $11.5k–$13k | $7k–$8.5k |
| Cleveland to ChicagoCleveland, OH306 mi · 1h 00m light | 306 mi | 1h 00mlight | $7.5k–$9k | $9k–$9.5k | $10.5k–$12k | $12k–$13.5k | $7.5k–$9k |
| Minneapolis to ChicagoMinneapolis, MN348 mi · 1h 05m light | 348 mi | 1h 05mlight | $8k–$10k | $9.5k–$10.5k | $11.5k–$13k | $13k–$15k | $8k–$10k |
| Kansas City to ChicagoKansas City, MO404 mi · 1h 10m light | 404 mi | 1h 10mlight | $9k–$11k | $11k–$11.5k | $13k–$14.5k | $14.5k–$16.5k | $9k–$11k |
| Omaha to ChicagoOmaha, NE422 mi · 1h 15m light | 422 mi | 1h 15mlight | $9.5k–$11.5k | $11k–$12k | $13.5k–$15k | $15k–$17k | $9.5k–$11.5k |
Southeast17 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Louisville to ChicagoLouisville, KY272 mi · 55m light | 272 mi | 55mlight | $7k–$8.5k | $8k–$9k | $10k–$11k | $11k–$12.5k | $7k–$8.5k |
| Nashville to ChicagoNashville, TN395 mi · 1h 10m light | 395 mi | 1h 10mlight | $9k–$11k | $10.5k–$11.5k | $12.5k–$14.5k | $14.5k–$16.5k | $9k–$11k |
| Knoxville to ChicagoKnoxville, TN460 mi · 1h 20m light | 460 mi | 1h 20mlight | $10k–$12.5k | $12k–$13k | $14k–$16k | $16k–$18.5k | $10k–$12.5k |
| Memphis to ChicagoMemphis, TN481 mi · 1h 20m light | 481 mi | 1h 20mlight | $10.5k–$13k | $12.5k–$13k | $14.5k–$16.5k | $16.5k–$19k | $10.5k–$13k |
| Chattanooga to ChicagoChattanooga, TN486 mi · 1h 25m light | 486 mi | 1h 25mlight | $10.5k–$13k | $12.5k–$13.5k | $15k–$16.5k | $17k–$19k | $10.5k–$13k |
| Little Rock to ChicagoLittle Rock, AR544 mi · 1h 30m light | 544 mi | 1h 30mlight | $11.5k–$14k | $13.5k–$14.5k | $16k–$18k | $18.5k–$21k | $11.5k–$14k |
| Greenville, SC to ChicagoGreenville, SC, SC562 mi · 1h 35m light | 562 mi | 1h 35mlight | $11.5k–$14.5k | $14k–$15k | $16.5k–$18.5k | $19k–$21.5k | $11.5k–$14.5k |
| Birmingham to ChicagoBirmingham, AL571 mi · 1h 35m light | 571 mi | 1h 35mlight | $12k–$14.5k | $14k–$15k | $16.5k–$19k | $19k–$21.5k | $12k–$14.5k |
| Greensboro to ChicagoGreensboro, NC575 mi · 1h 35m light | 575 mi | 1h 35mlight | $12k–$15k | $14k–$15k | $17k–$19k | $19k–$22k | $12k–$15k |
| Atlanta to ChicagoAtlanta, GA578 mi · 1h 35m light | 578 mi | 1h 35mlight | $12k–$15k | $14k–$15.5k | $17k–$19k | $19k–$22k | $12k–$15k |
| Charlotte to ChicagoCharlotte, NC584 mi · 1h 35m light | 584 mi | 1h 35mlight | $12k–$15k | $14.5k–$15.5k | $17k–$19k | $19.5k–$22k | $12k–$15k |
| Raleigh-Durham to ChicagoRaleigh-Durham, NC631 mi · 1h 40m light | 631 mi | 1h 40mlight | $13k–$16k | $15.5k–$16.5k | $18k–$20.5k | $20.5k–$23.5k | $13k–$16k |
| Myrtle Beach to ChicagoMyrtle Beach, SC738 mi · 1h 55m light | 738 mi | 1h 55mlight | $14.5k–$18k | $17.5k–$18.5k | $20.5k–$23.5k | $23.5k–$26.5k | $14.5k–$18k |
| Charleston to ChicagoCharleston, SC745 mi · 2h 00m light | 745 mi | 2h 00mlight | $14.5k–$18.5k | $17.5k–$19k | $21k–$23.5k | $23.5k–$27k | $14.5k–$18.5k |
| Savannah to ChicagoSavannah, GA759 mi · 2h 00m light | 759 mi | 2h 00mlight | $15k–$18.5k | $18k–$19k | $21k–$24k | $24k–$27k | $15k–$18.5k |
| Hilton Head to ChicagoHilton Head, SC766 mi · 2h 00m light | 766 mi | 2h 00mlight | $15k–$19k | $18k–$19k | $21.5k–$24k | $24k–$27.5k | $15k–$19k |
| New Orleans to ChicagoNew Orleans, LA827 mi · 2h 10m light | 827 mi | 2h 10mlight | $16k–$20k | $19k–$20.5k | $22.5k–$25.5k | $25.5k–$29.5k | $16k–$20k |
Northeast17 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Pittsburgh to ChicagoPittsburgh, PA401 mi · 1h 10m light | 401 mi | 1h 10mlight | $9k–$11k | $11k–$11.5k | $13k–$14.5k | $14.5k–$16.5k | $9k–$11k |
| Buffalo to ChicagoBuffalo, NY467 mi · 1h 20m light | 467 mi | 1h 20mlight | $10k–$12.5k | $12k–$13k | $14.5k–$16k | $16.5k–$18.5k | $10k–$12.5k |
| Rochester to ChicagoRochester, NY522 mi · 1h 30m light | 522 mi | 1h 30mlight | $11k–$13.5k | $13k–$14k | $15.5k–$17.5k | $17.5k–$20k | $11k–$13.5k |
| Philadelphia to ChicagoPhiladelphia, PA675 mi · 1h 50m light | 675 mi | 1h 50mlight | $13.5k–$17k | $16k–$17.5k | $19k–$21.5k | $21.5k–$24.5k | $13.5k–$17k |
| New York to ChicagoNew York, NY713 mi · 1h 55m light | 713 mi | 1h 55mlight | $14k–$17.5k | $17k–$18k | $20k–$22.5k | $22.5k–$26k | $14k–$17.5k |
| Albany to ChicagoAlbany, NY716 mi · 1h 55m light | 716 mi | 1h 55mlight | $14k–$17.5k | $17k–$18k | $20k–$22.5k | $23k–$26k | $14k–$17.5k |
| New Haven to ChicagoNew Haven, CT769 mi · 2h 00m light | 769 mi | 2h 00mlight | $15k–$19k | $18k–$19.5k | $21.5k–$24k | $24k–$27.5k | $15k–$19k |
| Hartford to ChicagoHartford, CT774 mi · 2h 00m light | 774 mi | 2h 00mlight | $15k–$19k | $18k–$19.5k | $21.5k–$24k | $24.5k–$27.5k | $15k–$19k |
| Lebanon, NH to ChicagoLebanon, NH, NH793 mi · 2h 05m light | 793 mi | 2h 05mlight | $15.5k–$19.5k | $18.5k–$20k | $22k–$24.5k | $25k–$28.5k | $15.5k–$19.5k |
| The Hamptons to ChicagoThe Hamptons, NY805 mi · 2h 05m light | 805 mi | 2h 05mlight | $15.5k–$19.5k | $18.5k–$20k | $22k–$25k | $25k–$28.5k | $15.5k–$19.5k |
| Manchester, NH to ChicagoManchester, NH, NH835 mi · 2h 10m light | 835 mi | 2h 10mlight | $16k–$20k | $19.5k–$20.5k | $23k–$26k | $26k–$29.5k | $16k–$20k |
| Providence to ChicagoProvidence, RI840 mi · 2h 10m light | 840 mi | 2h 10mlight | $16.5k–$20.5k | $19.5k–$21k | $23k–$26k | $26k–$29.5k | $16.5k–$20.5k |
| Boston to ChicagoBoston, MA844 mi · 2h 10m light | 844 mi | 2h 10mlight | $16.5k–$20.5k | $19.5k–$21k | $23k–$26k | $26k–$30k | $16.5k–$20.5k |
| Martha's Vineyard to ChicagoMartha's Vineyard, MA885 mi · 2h 15m light | 885 mi | 2h 15mlight | $17k–$21k | $20.5k–$21.5k | $24k–$27k | $27k–$31k | $17k–$21k |
| Portland, Maine to ChicagoPortland, Maine, ME893 mi · 2h 15m light | 893 mi | 2h 15mlight | $17k–$21.5k | $20.5k–$22k | $24k–$27.5k | $27.5k–$31k | $17k–$21.5k |
| Nantucket to ChicagoNantucket, MA914 mi · 2h 20m light | 914 mi | 2h 20mlight | $17.5k–$22k | $21k–$22k | $24.5k–$28k | $28k–$32k | $17.5k–$22k |
| Bangor to ChicagoBangor, ME972 mi · 2h 30m light | 972 mi | 2h 30mlight | $18.5k–$23k | $22k–$23.5k | $26k–$29.5k | $29.5k–$33.5k | $18.5k–$23k |
Canada10 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Toronto to ChicagoToronto, Canada432 mi · 1h 15m light | 432 mi | 1h 15mlight | $9.5k–$12k | $11.5k–$12k | $13.5k–$15.5k | $15.5k–$17.5k | $9.5k–$12k |
| Ottawa to ChicagoOttawa, Canada652 mi · 1h 45m light | 652 mi | 1h 45mlight | $13k–$16.5k | $15.5k–$17k | $18.5k–$21k | $21k–$24k | $13k–$16.5k |
| Winnipeg to ChicagoWinnipeg, Canada722 mi · 1h 55m light | 722 mi | 1h 55mlight | $14.5k–$18k | $17k–$18.5k | $20k–$23k | $23k–$26k | $14.5k–$18k |
| Montreal to ChicagoMontreal, Canada744 mi · 1h 55m light | 744 mi | 1h 55mlight | $14.5k–$18.5k | $17.5k–$19k | $20.5k–$23.5k | $23.5k–$27k | $14.5k–$18.5k |
| Quebec City to ChicagoQuebec City, Canada878 mi · 2h 15m light | 878 mi | 2h 15mlight | $17k–$21k | $20k–$21.5k | $24k–$27k | $27k–$31k | $17k–$21k |
| Halifax to ChicagoHalifax, Canada1,232 mi · 2h 50m midsize | 1,232 mi | 2h 50mmidsize | $23k–$28.5k | $26.5k–$29k | $32k–$36.5k | $36.5k–$41.5k | $26.5k–$29k |
| Calgary to ChicagoCalgary, Canada1,396 mi · 3h 10m midsize | 1,396 mi | 3h 10mmidsize | $25.5k–$32k | $29k–$32k | $36k–$40.5k | $40.5k–$46k | $29k–$32k |
| Edmonton to ChicagoEdmonton, Canada1,431 mi · 3h 15m midsize | 1,431 mi | 3h 15mmidsize | $26k–$32.5k | $29.5k–$33k | $36.5k–$41.5k | $41.5k–$47.5k | $29.5k–$33k |
| Kelowna to ChicagoKelowna, Canada1,608 mi · 3h 40m midsize | 1,608 mi | 3h 40mmidsize | $29k–$36.5k | $32.5k–$36.5k | $41k–$46k | $46k–$53k | $32.5k–$36.5k |
| Vancouver to ChicagoVancouver, Canada1,773 mi · 4h 00m midsize | 1,773 mi | 4h 00mmidsize | $32k–$39.5k | $35.5k–$40k | $44.5k–$50k | $50k–$57k | $35.5k–$40k |
Mid-Atlantic4 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Washington, DC to ChicagoWashington, DC, DC576 mi · 1h 35m light | 576 mi | 1h 35mlight | $12k–$15k | $14k–$15k | $17k–$19k | $19k–$22k | $12k–$15k |
| Baltimore to ChicagoBaltimore, MD609 mi · 1h 40m light | 609 mi | 1h 40mlight | $12.5k–$15.5k | $15k–$16k | $17.5k–$20k | $20k–$23k | $12.5k–$15.5k |
| Richmond to ChicagoRichmond, VA628 mi · 1h 40m light | 628 mi | 1h 40mlight | $12.5k–$16k | $15k–$16.5k | $18k–$20.5k | $20.5k–$23.5k | $12.5k–$16k |
| Norfolk to ChicagoNorfolk, VA703 mi · 1h 50m light | 703 mi | 1h 50mlight | $14k–$17.5k | $16.5k–$18k | $20k–$22.5k | $22.5k–$25.5k | $14k–$17.5k |
Texas and Oklahoma10 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Tulsa to ChicagoTulsa, OK583 mi · 1h 35m light | 583 mi | 1h 35mlight | $12k–$15k | $14.5k–$15.5k | $17k–$19k | $19.5k–$22k | $12k–$15k |
| Oklahoma City to ChicagoOklahoma City, OK690 mi · 1h 50m light | 690 mi | 1h 50mlight | $14k–$17k | $16.5k–$17.5k | $19.5k–$22k | $22k–$25k | $14k–$17k |
| Dallas to ChicagoDallas, TX794 mi · 2h 05m light | 794 mi | 2h 05mlight | $15.5k–$19.5k | $18.5k–$20k | $22k–$24.5k | $25k–$28.5k | $15.5k–$19.5k |
| Amarillo to ChicagoAmarillo, TX879 mi · 2h 15m light | 879 mi | 2h 15mlight | $17k–$21k | $20k–$21.5k | $24k–$27k | $27k–$31k | $17k–$21k |
| Houston to ChicagoHouston, TX938 mi · 2h 25m light | 938 mi | 2h 25mlight | $18k–$22.5k | $21.5k–$22.5k | $25.5k–$28.5k | $28.5k–$32.5k | $18k–$22.5k |
| Lubbock to ChicagoLubbock, TX950 mi · 2h 25m light | 950 mi | 2h 25mlight | $18k–$22.5k | $21.5k–$23k | $25.5k–$29k | $29k–$33k | $18k–$22.5k |
| Austin to ChicagoAustin, TX972 mi · 2h 30m light | 972 mi | 2h 30mlight | $18.5k–$23k | $22k–$23.5k | $26k–$29.5k | $29.5k–$33.5k | $18.5k–$23k |
| San Antonio to ChicagoSan Antonio, TX1,037 mi · 2h 25m midsize | 1,037 mi | 2h 25mmidsize | $19.5k–$24.5k | $23.5k–$24.5k | $27.5k–$31k | $31k–$35.5k | $23.5k–$24.5k |
| Midland to ChicagoMidland, TX1,046 mi · 2h 30m midsize | 1,046 mi | 2h 30mmidsize | $19.5k–$24.5k | $23.5k–$25k | $28k–$31.5k | $31.5k–$36k | $23.5k–$25k |
| El Paso to ChicagoEl Paso, TX1,235 mi · 2h 50m midsize | 1,235 mi | 2h 50mmidsize | $23k–$28.5k | $26.5k–$29k | $32k–$36.5k | $36.5k–$41.5k | $26.5k–$29k |
Florida11 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Pensacola to ChicagoPensacola, FL782 mi · 2h 05m light | 782 mi | 2h 05mlight | $15.5k–$19k | $18.5k–$19.5k | $21.5k–$24.5k | $24.5k–$28k | $15.5k–$19k |
| Destin to ChicagoDestin, FL784 mi · 2h 05m light | 784 mi | 2h 05mlight | $15.5k–$19k | $18.5k–$19.5k | $21.5k–$24.5k | $24.5k–$28k | $15.5k–$19k |
| Jacksonville to ChicagoJacksonville, FL850 mi · 2h 10m light | 850 mi | 2h 10mlight | $16.5k–$20.5k | $19.5k–$21k | $23k–$26k | $26.5k–$30k | $16.5k–$20.5k |
| Orlando to ChicagoOrlando, FL983 mi · 2h 30m light | 983 mi | 2h 30mlight | $18.5k–$23.5k | $22k–$23.5k | $26.5k–$29.5k | $30k–$34k | $18.5k–$23.5k |
| Tampa to ChicagoTampa, FL998 mi · 2h 20m midsize | 998 mi | 2h 20mmidsize | $19k–$23.5k | $22.5k–$24k | $26.5k–$30k | $30k–$34.5k | $22.5k–$24k |
| Sarasota to ChicagoSarasota, FL1,037 mi · 2h 25m midsize | 1,037 mi | 2h 25mmidsize | $19.5k–$24.5k | $23.5k–$24.5k | $27.5k–$31k | $31k–$35.5k | $23.5k–$24.5k |
| Vero Beach to ChicagoVero Beach, FL1,060 mi · 2h 30m midsize | 1,060 mi | 2h 30mmidsize | $20k–$25k | $23.5k–$25k | $28k–$32k | $32k–$36k | $23.5k–$25k |
| Palm Beach to ChicagoPalm Beach, FL1,130 mi · 2h 40m midsize | 1,130 mi | 2h 40mmidsize | $21k–$26.5k | $25k–$26.5k | $29.5k–$33.5k | $33.5k–$38.5k | $25k–$26.5k |
| Naples to ChicagoNaples, FL1,132 mi · 2h 40m midsize | 1,132 mi | 2h 40mmidsize | $21k–$26.5k | $25k–$26.5k | $30k–$33.5k | $33.5k–$38.5k | $25k–$26.5k |
| Miami to ChicagoMiami, FL1,177 mi · 2h 45m midsize | 1,177 mi | 2h 45mmidsize | $22k–$27.5k | $25.5k–$27.5k | $31k–$35k | $35k–$39.5k | $25.5k–$27.5k |
| Key West to ChicagoKey West, FL1,239 mi · 2h 50m midsize | 1,239 mi | 2h 50mmidsize | $23k–$28.5k | $26.5k–$29k | $32k–$36.5k | $36.5k–$41.5k | $26.5k–$29k |
Mountain West11 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Denver to ChicagoDenver, CO907 mi · 2h 20m light | 907 mi | 2h 20mlight | $17.5k–$21.5k | $20.5k–$22k | $24.5k–$27.5k | $28k–$31.5k | $17.5k–$21.5k |
| Colorado Springs to ChicagoColorado Springs, CO915 mi · 2h 20m light | 915 mi | 2h 20mlight | $17.5k–$22k | $21k–$22k | $24.5k–$28k | $28k–$32k | $17.5k–$22k |
| Vail to ChicagoVail, CO1,012 mi · 2h 25m midsize | 1,012 mi | 2h 25mmidsize | $19k–$24k | $23k–$24k | $27k–$30.5k | $30.5k–$35k | $23k–$24k |
| Steamboat Springs to ChicagoSteamboat Springs, CO1,015 mi · 2h 25m midsize | 1,015 mi | 2h 25mmidsize | $19k–$24k | $23k–$24k | $27k–$30.5k | $30.5k–$35k | $23k–$24k |
| Aspen to ChicagoAspen, CO1,018 mi · 2h 25m midsize | 1,018 mi | 2h 25mmidsize | $19.5k–$24k | $23k–$24.5k | $27k–$30.5k | $30.5k–$35k | $23k–$24.5k |
| Telluride to ChicagoTelluride, CO1,098 mi · 2h 35m midsize | 1,098 mi | 2h 35mmidsize | $20.5k–$25.5k | $24.5k–$26k | $29k–$33k | $33k–$37.5k | $24.5k–$26k |
| Jackson Hole to ChicagoJackson Hole, WY1,170 mi · 2h 45m midsize | 1,170 mi | 2h 45mmidsize | $22k–$27k | $25.5k–$27.5k | $30.5k–$34.5k | $34.5k–$39.5k | $25.5k–$27.5k |
| Bozeman to ChicagoBozeman, MT1,195 mi · 2h 45m midsize | 1,195 mi | 2h 45mmidsize | $22k–$27.5k | $26k–$28k | $31k–$35.5k | $35.5k–$40k | $26k–$28k |
| Salt Lake City to ChicagoSalt Lake City, UT1,256 mi · 2h 55m midsize | 1,256 mi | 2h 55mmidsize | $23k–$29k | $27k–$29.5k | $32.5k–$37k | $37k–$42k | $27k–$29.5k |
| Sun Valley to ChicagoSun Valley, ID1,348 mi · 3h 05m midsize | 1,348 mi | 3h 05mmidsize | $25k–$31k | $28.5k–$31k | $35k–$39.5k | $39.5k–$45k | $28.5k–$31k |
| Boise to ChicagoBoise, ID1,444 mi · 3h 15m midsize | 1,444 mi | 3h 15mmidsize | $26.5k–$33k | $30k–$33k | $37k–$42k | $42k–$47.5k | $30k–$33k |
Southwest5 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Santa Fe to ChicagoSanta Fe, NM1,074 mi · 2h 30m midsize | 1,074 mi | 2h 30mmidsize | $20k–$25k | $24k–$25.5k | $28.5k–$32k | $32k–$36.5k | $24k–$25.5k |
| Albuquerque to ChicagoAlbuquerque, NM1,119 mi · 2h 35m midsize | 1,119 mi | 2h 35mmidsize | $21k–$26k | $24.5k–$26.5k | $29.5k–$33.5k | $33.5k–$38k | $24.5k–$26.5k |
| Scottsdale to ChicagoScottsdale, AZ1,430 mi · 3h 15m midsize | 1,430 mi | 3h 15mmidsize | $26k–$32.5k | $29.5k–$33k | $36.5k–$41.5k | $41.5k–$47k | $29.5k–$33k |
| Tucson to ChicagoTucson, AZ1,438 mi · 3h 15m midsize | 1,438 mi | 3h 15mmidsize | $26.5k–$33k | $30k–$33k | $37k–$41.5k | $41.5k–$47.5k | $30k–$33k |
| Las Vegas to ChicagoLas Vegas, NV1,517 mi · 3h 25m midsize | 1,517 mi | 3h 25mmidsize | $27.5k–$34.5k | $31k–$34.5k | $38.5k–$44k | $43.5k–$50k | $31k–$34.5k |
Bahamas, Caribbean and Bermuda32 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Grand Bahama to ChicagoGrand Bahama, Bahamas1,171 mi · 2h 45m midsize | 1,171 mi | 2h 45mmidsize | $22k–$27k | $25.5k–$27.5k | $30.5k–$34.5k | $34.5k–$39.5k | $25.5k–$27.5k |
| Bimini to ChicagoBimini, Bahamas1,212 mi · 2h 50m midsize | 1,212 mi | 2h 50mmidsize | $22.5k–$28k | $26k–$28.5k | $31.5k–$35.5k | $35.5k–$41k | $26k–$28.5k |
| Abaco to ChicagoAbaco, Bahamas1,217 mi · 2h 50m midsize | 1,217 mi | 2h 50mmidsize | $22.5k–$28k | $26.5k–$28.5k | $31.5k–$36k | $36k–$41k | $26.5k–$28.5k |
| Eleuthera to ChicagoEleuthera, Bahamas1,292 mi · 3h 00m midsize | 1,292 mi | 3h 00mmidsize | $24k–$29.5k | $27.5k–$30k | $33.5k–$38k | $38k–$43k | $27.5k–$30k |
| Nassau to ChicagoNassau, Bahamas1,298 mi · 3h 00m midsize | 1,298 mi | 3h 00mmidsize | $24k–$30k | $27.5k–$30k | $33.5k–$38k | $38k–$43.5k | $27.5k–$30k |
| Bermuda to ChicagoBermuda1,423 mi · 3h 15m midsize | 1,423 mi | 3h 15mmidsize | $26k–$32.5k | $29.5k–$32.5k | $36k–$41.5k | $41.5k–$47k | $29.5k–$32.5k |
| Exuma to ChicagoExuma, Bahamas1,433 mi · 3h 15m midsize | 1,433 mi | 3h 15mmidsize | $26k–$32.5k | $29.5k–$33k | $36.5k–$41.5k | $41.5k–$47.5k | $29.5k–$33k |
| Grand Cayman to ChicagoGrand Cayman, Cayman Islands1,599 mi · 3h 35m midsize | 1,599 mi | 3h 35mmidsize | $29k–$36k | $32.5k–$36.5k | $40.5k–$46k | $46k–$52k | $32.5k–$36.5k |
| Turks & Caicos to ChicagoTurks & Caicos1,649 mi · 3h 45m midsize | 1,649 mi | 3h 45mmidsize | $30k–$37k | $33.5k–$37.5k | $42k–$47k | $47k–$54k | $33.5k–$37.5k |
| Montego Bay to ChicagoMontego Bay, Jamaica1,710 mi · 3h 50m midsize | 1,710 mi | 3h 50mmidsize | $31k–$38.5k | $34.5k–$38.5k | $43k–$49k | $49k–$56k | $34.5k–$38.5k |
| Kingston to ChicagoKingston, Jamaica1,770 mi · 4h 00m midsize | 1,770 mi | 4h 00mmidsize | $32k–$39.5k | $35.5k–$40k | $44.5k–$50k | $50k–$57k | $35.5k–$40k |
| Puerto Plata to ChicagoPuerto Plata, Dominican Republic1,824 mi · 4h 05m midsize | 1,824 mi | 4h 05mmidsize | $32.5k–$41k | $36.5k–$41k | $46k–$52k | $52k–$59k | $36.5k–$41k |
| Santiago to ChicagoSantiago, Dominican Republic1,845 mi · 4h 05m midsize | 1,845 mi | 4h 05mmidsize | $33k–$41k | $37k–$41.5k | $46.5k–$52k | $52k–$60k | $37k–$41.5k |
| Santo Domingo to ChicagoSanto Domingo, Dominican Republic1,933 mi · 4h 20m midsize | 1,933 mi | 4h 20mmidsize | $34.5k–$43k | $38.5k–$43.5k | $48.5k–$55k | $55k–$62k | $38.5k–$43.5k |
| La Romana to ChicagoLa Romana, Dominican Republic1,957 mi · 4h 20m midsize | 1,957 mi | 4h 20mmidsize | $37k–$46.5k+1 stop | $39k–$44k | $49k–$55k | $55k–$63k | $39k–$44k |
| Punta Cana to ChicagoPunta Cana, Dominican Republic1,968 mi · 4h 20m midsize | 1,968 mi | 4h 20mmidsize | $37.5k–$46.5k+1 stop | $39k–$44k | $49k–$56k | $56k–$63k | $39k–$44k |
| San Juan to ChicagoSan Juan, Puerto Rico2,059 mi · 4h 30m super-midsize | 2,059 mi | 4h 30msuper-midsize | $39k–$48.5k+1 stop | $41k–$46k | $51k–$58k | $58k–$66k | $51k–$58k |
| St Thomas to ChicagoSt Thomas, U.S. Virgin Islands2,103 mi · 4h 35m super-midsize | 2,103 mi | 4h 35msuper-midsize | $39.5k–$49.5k+1 stop | $41.5k–$47k | $52k–$59k | $59k–$67k | $52k–$59k |
| Tortola to ChicagoTortola, British Virgin Islands2,113 mi · 4h 35m super-midsize | 2,113 mi | 4h 35msuper-midsize | $40k–$49.5k+1 stop | $42k–$47k | $53k–$59k | $59k–$68k | $53k–$59k |
| St Croix to ChicagoSt Croix, U.S. Virgin Islands2,145 mi · 4h 40m super-midsize | 2,145 mi | 4h 40msuper-midsize | $40.5k–$50k+1 stop | $42.5k–$48k | $53k–$60k | $60k–$69k | $53k–$60k |
| Anguilla to ChicagoAnguilla2,184 mi · 4h 45m super-midsize | 2,184 mi | 4h 45msuper-midsize | $41k–$51k+1 stop | $43k–$48.5k | $54k–$61k | $61k–$70k | $54k–$61k |
| St Barths to ChicagoSt Barths, French West Indies2,191 mi · 4h 45m super-midsize | 2,191 mi | 4h 45msuper-midsize | $41k–$51k+1 stop | $43.5k–$49k | $54k–$61k | $61k–$70k | $54k–$61k |
| St Kitts to ChicagoSt Kitts, St Kitts & Nevis2,246 mi · 4h 50m super-midsize | 2,246 mi | 4h 50msuper-midsize | $42k–$52k+1 stop | $44.5k–$50k | $56k–$63k | $63k–$72k | $56k–$63k |
| Aruba to ChicagoAruba2,288 mi · 4h 55m super-midsize | 2,288 mi | 4h 55msuper-midsize | $42.5k–$53k+1 stop | $45k–$51k | $57k–$64k | $64k–$73k | $57k–$64k |
| Antigua to ChicagoAntigua, Antigua & Barbuda2,292 mi · 4h 55m super-midsize | 2,292 mi | 4h 55msuper-midsize | $43k–$53k+1 stop | $45k–$51k | $57k–$64k | $64k–$73k | $57k–$64k |
| Curaçao to ChicagoCuraçao2,338 mi · 5h 00m super-midsize | 2,338 mi | 5h 00msuper-midsize | $43.5k–$54k+1 stop | $49k–$55k+1 stop | $58k–$65k | $65k–$74k | $58k–$65k |
| Bonaire to ChicagoBonaire2,362 mi · 5h 05m super-midsize | 2,362 mi | 5h 05msuper-midsize | $44k–$55k+1 stop | $49k–$55k+1 stop | $58k–$66k | $66k–$75k | $58k–$66k |
| St Lucia to ChicagoSt Lucia2,516 mi · 5h 25m super-midsize | 2,516 mi | 5h 25msuper-midsize | $46.5k–$58k+1 stop | $52k–$59k+1 stop | $62k–$70k | $70k–$80k | $62k–$70k |
| St Vincent to ChicagoSt Vincent, St Vincent & the Grenadines2,542 mi · 5h 25m super-midsize | 2,542 mi | 5h 25msuper-midsize | $47k–$59k+1 stop | $53k–$59k+1 stop | $63k–$71k | $71k–$80k | $63k–$71k |
| Grenada to ChicagoGrenada2,585 mi · 5h 30m super-midsize | 2,585 mi | 5h 30msuper-midsize | $47.5k–$59k+1 stop | $53k–$60k+1 stop | $64k–$72k | $72k–$82k | $64k–$72k |
| Barbados to ChicagoBarbados2,610 mi · 5h 35m super-midsize | 2,610 mi | 5h 35msuper-midsize | $48k–$60k+1 stop | $54k–$61k+1 stop | $64k–$72k | $72k–$82k | $64k–$72k |
| Trinidad to ChicagoTrinidad, Trinidad & Tobago2,683 mi · 5h 45m super-midsize | 2,683 mi | 5h 45msuper-midsize | $49.5k–$62k+1 stop | $55k–$62k+1 stop | $66k–$74k | $74k–$85k | $66k–$74k |
Mexico13 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Monterrey to ChicagoMonterrey, Mexico1,311 mi · 3h 00m midsize | 1,311 mi | 3h 00mmidsize | $24k–$30k | $28k–$30.5k | $34k–$38.5k | $38.5k–$43.5k | $28k–$30.5k |
| Cancún to ChicagoCancún, Mexico1,434 mi · 3h 15m midsize | 1,434 mi | 3h 15mmidsize | $26k–$32.5k | $29.5k–$33k | $37k–$41.5k | $41.5k–$47.5k | $29.5k–$33k |
| Mérida to ChicagoMérida, Mexico1,445 mi · 3h 15m midsize | 1,445 mi | 3h 15mmidsize | $26.5k–$33k | $30k–$33k | $37k–$42k | $42k–$47.5k | $30k–$33k |
| Cozumel to ChicagoCozumel, Mexico1,470 mi · 3h 20m midsize | 1,470 mi | 3h 20mmidsize | $27k–$33.5k | $30.5k–$33.5k | $37.5k–$42.5k | $42.5k–$48.5k | $30.5k–$33.5k |
| Querétaro to ChicagoQuerétaro, Mexico1,633 mi · 3h 40m midsize | 1,633 mi | 3h 40mmidsize | $29.5k–$37k | $33k–$37k | $41.5k–$47k | $46.5k–$53k | $33k–$37k |
| León to ChicagoLeón, Mexico1,644 mi · 3h 40m midsize | 1,644 mi | 3h 40mmidsize | $29.5k–$37k | $33k–$37.5k | $41.5k–$47k | $47k–$54k | $33k–$37.5k |
| Mexico City to ChicagoMexico City, Mexico1,699 mi · 3h 50m midsize | 1,699 mi | 3h 50mmidsize | $30.5k–$38k | $34k–$38.5k | $43k–$48.5k | $48.5k–$55k | $34k–$38.5k |
| Guadalajara to ChicagoGuadalajara, Mexico1,727 mi · 3h 50m midsize | 1,727 mi | 3h 50mmidsize | $31k–$39k | $34.5k–$39k | $43.5k–$49.5k | $49k–$56k | $34.5k–$39k |
| Puerto Vallarta to ChicagoPuerto Vallarta, Mexico1,780 mi · 4h 00m midsize | 1,780 mi | 4h 00mmidsize | $32k–$40k | $35.5k–$40k | $45k–$51k | $51k–$58k | $35.5k–$40k |
| Oaxaca to ChicagoOaxaca, Mexico1,793 mi · 4h 00m midsize | 1,793 mi | 4h 00mmidsize | $32k–$40k | $36k–$40.5k | $45k–$51k | $51k–$58k | $36k–$40.5k |
| Los Cabos to ChicagoLos Cabos, Mexico1,805 mi · 4h 00m midsize | 1,805 mi | 4h 00mmidsize | $32.5k–$40.5k | $36k–$40.5k | $45.5k–$51k | $51k–$58k | $36k–$40.5k |
| Zihuatanejo to ChicagoZihuatanejo, Mexico1,857 mi · 4h 10m midsize | 1,857 mi | 4h 10mmidsize | $33.5k–$41.5k | $37k–$42k | $46.5k–$53k | $53k–$60k | $37k–$42k |
| Acapulco to ChicagoAcapulco, Mexico1,870 mi · 4h 10m midsize | 1,870 mi | 4h 10mmidsize | $33.5k–$42k | $37.5k–$42k | $47k–$53k | $53k–$60k | $37.5k–$42k |
West Coast9 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Palm Springs to ChicagoPalm Springs, CA1,654 mi · 3h 45m midsize | 1,654 mi | 3h 45mmidsize | $30k–$37.5k | $33.5k–$37.5k | $42k–$47.5k | $47.5k–$54k | $33.5k–$37.5k |
| Lake Tahoe to ChicagoLake Tahoe, CA1,699 mi · 3h 50m midsize | 1,699 mi | 3h 50mmidsize | $30.5k–$38k | $34k–$38.5k | $43k–$48.5k | $48.5k–$55k | $34k–$38.5k |
| San Diego to ChicagoSan Diego, CA1,725 mi · 3h 50m midsize | 1,725 mi | 3h 50mmidsize | $31k–$39k | $34.5k–$39k | $43.5k–$49k | $49k–$56k | $34.5k–$39k |
| Seattle to ChicagoSeattle, WA1,728 mi · 3h 55m midsize | 1,728 mi | 3h 55mmidsize | $31k–$39k | $35k–$39k | $43.5k–$49.5k | $49k–$56k | $35k–$39k |
| Los Angeles to ChicagoLos Angeles, CA1,743 mi · 3h 55m midsize | 1,743 mi | 3h 55mmidsize | $31.5k–$39k | $35k–$39.5k | $44k–$49.5k | $49.5k–$57k | $35k–$39.5k |
| Portland to ChicagoPortland, OR1,747 mi · 3h 55m midsize | 1,747 mi | 3h 55mmidsize | $31.5k–$39k | $35k–$39.5k | $44k–$50k | $49.5k–$57k | $35k–$39.5k |
| Santa Barbara to ChicagoSanta Barbara, CA1,805 mi · 4h 00m midsize | 1,805 mi | 4h 00mmidsize | $32.5k–$40.5k | $36k–$40.5k | $45.5k–$51k | $51k–$58k | $36k–$40.5k |
| Monterey to ChicagoMonterey, CA1,848 mi · 4h 05m midsize | 1,848 mi | 4h 05mmidsize | $33k–$41.5k | $37k–$41.5k | $46.5k–$52k | $52k–$60k | $37k–$41.5k |
| San Francisco to ChicagoSan Francisco, CA1,850 mi · 4h 10m midsize | 1,850 mi | 4h 10mmidsize | $33k–$41.5k | $37k–$41.5k | $46.5k–$53k | $52k–$60k | $37k–$41.5k |
Central America8 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Belize City to ChicagoBelize City, Belize1,676 mi · 3h 45m midsize | 1,676 mi | 3h 45mmidsize | $30.5k–$37.5k | $34k–$38k | $42k–$48k | $48k–$55k | $34k–$38k |
| Roatán to ChicagoRoatán, Honduras1,761 mi · 3h 55m midsize | 1,761 mi | 3h 55mmidsize | $31.5k–$39.5k | $35.5k–$40k | $44k–$50k | $50k–$57k | $35.5k–$40k |
| Guatemala City to ChicagoGuatemala City, Guatemala1,887 mi · 4h 10m midsize | 1,887 mi | 4h 10mmidsize | $34k–$42k | $37.5k–$42.5k | $47k–$54k | $53k–$61k | $37.5k–$42.5k |
| San Salvador to ChicagoSan Salvador, El Salvador1,960 mi · 4h 20m midsize | 1,960 mi | 4h 20mmidsize | $37k–$46.5k+1 stop | $39k–$44k | $48.5k–$56k | $55k–$63k | $39k–$44k |
| Managua to ChicagoManagua, Nicaragua2,050 mi · 4h 25m super-midsize | 2,050 mi | 4h 25msuper-midsize | $39k–$48.5k+1 stop | $41k–$46k | $51k–$58k | $58k–$66k | $51k–$58k |
| Guanacaste to ChicagoGuanacaste, Costa Rica2,159 mi · 4h 40m super-midsize | 2,159 mi | 4h 40msuper-midsize | $40.5k–$51k+1 stop | $43k–$48k | $53k–$61k | $61k–$69k | $53k–$61k |
| San José to ChicagoSan José, Costa Rica2,207 mi · 4h 45m super-midsize | 2,207 mi | 4h 45msuper-midsize | $41.5k–$52k+1 stop | $43.5k–$49k | $54k–$62k | $62k–$70k | $54k–$62k |
| Panama City to ChicagoPanama City, Panama2,317 mi · 5h 00m super-midsize | 2,317 mi | 5h 00msuper-midsize | $43k–$54k+1 stop | $48.5k–$54k+1 stop | $57k–$65k | $65k–$74k | $57k–$65k |
Hawaii and Alaska7 routes
| Route | Distance | Flight time | Light | Midsize | Super-mid | Large | One way, est. |
|---|---|---|---|---|---|---|---|
| Juneau to ChicagoJuneau, AK2,307 mi · 5h 00m super-midsize | 2,307 mi | 5h 00msuper-midsize | $43k–$54k+1 stop | $48k–$54k+1 stop | $57k–$65k | $64k–$73k | $57k–$65k |
| Fairbanks to ChicagoFairbanks, AK2,794 mi · 5h 55m super-midsize | 2,794 mi | 5h 55msuper-midsize | $51k–$64k+1 stop | $57k–$64k+1 stop | $68k–$78k | $77k–$88k | $68k–$78k |
| Anchorage to ChicagoAnchorage, AK2,854 mi · 6h 05m super-midsize | 2,854 mi | 6h 05msuper-midsize | $52k–$65k+1 stop | $58k–$66k+1 stop | $69k–$79k | $79k–$90k | $69k–$79k |
| Maui to ChicagoMaui, HI4,187 mi · 8h 25m large | 4,187 mi | 8h 25mlarge | — | — | $103k–$118k+1 stop | $114k–$129k | $114k–$129k |
| Kona to ChicagoKona, HI4,216 mi · 8h 25m large | 4,216 mi | 8h 25mlarge | — | — | $104k–$119k+1 stop | $114k–$130k | $114k–$130k |
| Honolulu to ChicagoHonolulu, HI4,246 mi · 8h 30m large | 4,246 mi | 8h 30mlarge | — | — | $105k–$120k+1 stop | $115k–$131k | $115k–$131k |
| Kauai to ChicagoKauai, HI4,291 mi · 8h 35m large | 4,291 mi | 8h 35mlarge | — | — | $106k–$121k+1 stop | $116k–$133k | $116k–$133k |
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